Holiday houses in Herald Harbor

Beautiful Waterfront Escape w/ Gorgeous Views

Escape to this stunning waterfront home on lovely Carr's Creek in Deale, MD. It offers four bedrooms and full bathrooms, two spacious living areas, two sunrooms, and a large fully stocked kitchen. You can birdwatch from the balcony, snuggle by the fireplace, soak in the hot tub, kayak, canoe, or play games and grill outdoors. Nearby, you can take a charter on the Chesapeake, kayak or hike at the Smithsonian Environmental Research Center, and enjoy local seafood restaurants and antique shopping.

Waterfront Chesapeake Bay Sunrises w/Private PIER!

Gorgeous sunrises and bay breezes await at this newly remodeled Chesapeake Bay waterfront cottage! Catch crabs or fish from your private pier, relax on the furnished deck, or explore Selby Bay with our complimentary canoe. Enjoy water views from the kitchen, dining, living room, and enclosed porch. Just 15 minutes from Annapolis & the Naval Academy, and 45 from DC—peaceful, clean, full of charm. Ideal for USNA families! Unplug, unwind, and make memories on the water—year-round relaxation & fun!

Blue on the Bay

2 bedroom cottage in historic Charlestown with screened porch, large yard & sitting area located in walking distance to the river and beach area. Walk to 3 local restaurants. Community playground, tennis courts, basketball court, pickle ball court, skate park & baseball field all in walking distance. Bring your boat, kayak & fishing poles. Boat launch available . Kayak, sup & pontoon rentals available. 15 minute drive to Great Wolfe Lodge. Monthly discount available, ask for details

Cottage #8 Herons Nest Lg 2 rooms Under Main House

OPEN March 25th to Nov 1st. every year. Herons Nest no 8 is located under main house, consist of full Kitchen, dining table, 1 queen size bed in separate bedroom, Living room Full size Futon open to a bed, 2 large sleeper recliners. Please call Jaimie upon arrival. No pets allowed! We no longer provide bed linens, Coffee, sugar or creams. or Towels. Boats are rentals! room tax 4% due on arrival , 6% Abb collects please Bring waters . Boat info below. If need air mattress can bring.

Chesapeake Cottages- 2 Quaint Waterfront Retreats

Our tastefully appointed cottages sit on almost an acre of waterfront property. Peaceful and tranquil, yet close to shops and restaurants, this property is perfect for serene getaways and family gatherings. With 2 separate cottages on one property, everyone will enjoy a unique and private space to relax. From peaceful mornings to magical sunsets on the 60-foot pier, this setting will quickly become a family favorite. This area is great for fishing, kayaking and paddle boarding!

"Riverside Retreat"

Welcome to your dream vacation in the historic city of Cambridge, Maryland! This charming well appointed Riverview rental is the perfect home base for exploring all that this fascinating city has to offer. With its rich history, vibrant culture, and stunning natural beauty, Cambridge is an ideal destination for relaxation and exploration. Within walking distance to great restaurants, shopping, marinas and a historic downtown area that will both entertain and delight you!

Cottage on Solitude Creek, Hot Tub, Pool & Firepit

Cottage on Solitude Creek, Hot Tub (open), Fire Pit, Pool (Not Heated -closed Oct-June) Convenient to St. Michaels, Easton, Oxford - this beautiful cottage has a fully equipped kitchen, patio with private hot tub and gas grill. Waterfront. Host resides on property, but will give you your privacy. *PLEASE NOTE: property complies with zoning of Talbot County which enforces a 3-night minimum and 4 guest max. NO DOGS ALLOWED No Parties #STRN-23-51

Waterfront Getaway w/ Pier - Sleeps 10, 4 bedrooms

Escape to our charming & serene waterfront retreat, perfectly situated on the picturesque Choptank River. This 4-bedroom home accommodates 10 guests w/ 7 comfortable beds & offers the ideal blend of relaxation & adventure. Our property comes fully equipped with bikes, kayaks, paddleboards & yard games for endless fun. Unwind and relax on the new pier. The river offers gorgeous sunrises and sunsets. Your perfect waterfront getaway awaits you!

Small, peaceful getaway

Approximately 10 miles from downtown Cambridge, MD. Relax in this newly remodeled home with nearby water access. (Choptank River & Chesapeake Bay)Quiet country setting with the amenities of home. Great location for biking, kayaking or sitting under the stars by the backyard firepit. Most days a family of deer can be seen in field across the road as well as Bald Eagles & Heron.